


Boys Interrupted

by kittenofdoomage



Category: Supernatural
Genre: Anal, Destiel - Freeform, F/M, M/F, M/M, Multi, NSFW, Oneshot, Oral, Reader Insert, Sex, Smut, Threesome, dp, explicit - Freeform, m/m - Freeform, m/m/f, moresome
Language: English
Status: Completed
Published: 2016-02-01
Updated: 2016-02-01
Packaged: 2018-05-17 16:47:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,871
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5878213
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: <blockquote class="userstuff">
              <p>Summary: The reader catches Dean and Castiel in a compromising position. She doesn't expect an invite.</p>
            </blockquote>





	Boys Interrupted

You’d only been on a quick run to the grocery store, whilst Sam was out interviewing witnesses for the latest case. Dean had complained of feeling ill, so you’d kindly offered to drop by the drug store to pick up some stuff for him whilst you were grabbing other supplies, and he’d appeared grateful, before sliding into his bed for some rest. So when you arrived back at the motel room, seeing that Sam was still absent, you didn’t expect to walk into the room you’d left a “poorly” Dean in, to hear _those_ kinds of noises. And you certainly weren’t expecting to see a shirtless Dean, on top of an equally shirtless Castiel, both kissing passionately. The covers for the bed were on the floor, along with the angel’s trenchcoat, shirt and Dean’s tee, and it was about 0.5 seconds before the bag of groceries you’d been carrying joined them.

Your mouth fell open at what you were witnessing, and you gasped, alerting both men to your presence. Cas’ face immediately flushed beet red, whilst Dean paused, then smirked at you. It wasn’t the first time you’d suspected this; the constant flirting and bromance between the two was hard to deny, but you’d never expected to find them doing _this_ , especially when Dean had seemed genuinely ill.

‘Yeah, you look real sick.’ You commented dryly, folding your arms as your shock turned to a glare in their direction. Dean’s smirk widened, and he pushed himself up to his knees. The angel on the bed glanced between the both of you, wondering what to do in this situation. 'Want me to leave you guys to it?’ Your question was pointed, and Cas flinched at your tone. Dean shrugged.

'If you like.’ He looked down at the half naked man on his bed, and the smirk turned into a sly grin. 'Or you could join us.’

Your shock returned ten fold and you spluttered a reply. 'W-what?’

Dean shrugged again, his green eyes zeroing in on you and practically turning your legs to jelly. 'Well, I mean, I’m not strictly one way or the other, and you’re not exactly bad on the eyes.’ You blinked, not sure what you were hearing. True, you’d harboured a crush on Dean Winchester since you’d laid eyes on his fine specimen of a body, and Cas was certainly pleasing to look at too, but you’d just walked in on _that_ (not that it wasn’t one of the hottest things you’d ever seen, and would probably fuel a few….a _lot_ of pleasant dreams) and surely they weren’t interested in sharing?

'Aren’t you guys….together?’

'No. We’re not.’ Cas said then, and it surprised you to hear it. He pushed Dean away a little so he could sit up. 'Not exclusively.’

'How do you even know what exclusively entails?’ You asked, and Dean chuckled, moving to stand, the muscles of his stomach rippling with the movement. Suddenly your mouth felt very dry, and you swallowed hard, trying to get some air into your lungs.

'Cas and me….it’s complicated. We…enjoy each other.’ The elder Winchester said, moving closer to you with each word. He was close enough to touch now, and his smile was enticing. 'And I’m not gonna lie – think you’d enjoy it too.’ He leaned in close, raising his eyebrows in that seductive way you’d seen him use on other women. 'Ever been with two guys at once?’ His hands were on the hem of his jeans, the top button undone, showing that delicious v-line dipping into his pants. You gulped, trying to move backwards, but you had nowhere to go except to bolt back out of the motel room. Dean quickly put a spot to that, reaching past you to shut the door. 'Come on, Y/N. You only live once.’

Your eyes darted between him and the half naked angel stood by the bed, and you thought it over for a moment. 'I…I…won’t it make things weird?’

'Only if you decide to mention anything to my little brother.’ Dean smirked again. 'But then, he might just get jealous he’s not joining in.’ He looked back over to Cas. 'Cas isn’t going to object, are ya?’ The angel shook his head.

'I’m certain this would be enjoyable. Dean has yet to be wrong about anything he’s shown me so far.’ Cas’ eyes traversed your body, and you were not feeling particularly sexy in your jeans and sweatshirt. But he smiled slowly, looking over to Dean. 'It would also be very educational. I’ve yet to know what it is like to be with a woman.’

'Well, that’s settled. Can’t let the poor guy go without knowing what that’s like, can we?’ Dean’s eyes were still on yours and you found yourself shaking your head, slightly bewildered at your own willingness to go along with this. But part of it was the curiosity of seeing _them_ together. Dean seemed to pick up on your thoughts as he got even closer, raising his hand to brush it through your loose hair, the slight touch of his fingertips on your collarbone making you jump a little. 'And I’ve always wondered what it would be like to fuck a guy whilst he’s fucking a girl.’ You shuddered at his lowered tone, closing your eyes. His free hand snaked around your waist to grasp your ass, pulling you in closer. 'Can’t imagine anything hotter than fucking Cas so hard it makes _you_ cum.’

And that was it. You were not leaving that room.

Goddamn him. Goddamn them both.

'Fuck.’ You whispered, just as Dean’s lips collided with yours and you sighed into his embrace. It ended too soon as he pulled away, gripping your wrist and guiding you towards the bed.

'Take your sweatshirt off and lay down.’ He ordered with a grin, and you raised an eyebrow.

'Kinda commandeering huh?’ You commented, taking a few steps towards the bed. Dean chuckled.

'You won’t be complaining in a minute. Cas?’ The angel was suddenly behind you, pulling at the hem of your jumper. You complied, allowing him to pull it over your head, your hair falling around your shoulders as his fingers moved to unhook your bra. He pushed the straps over your shoulders, leaving you naked from the waist up. Dean’s eyes roamed over you, making you feel self conscious for a moment. 'And I’m not complaining now.’ He said, coming towards you. He pushed you against Cas’ chest, kissing you as the angel behind you placed open mouthed kisses to your neck, his hands questing down around your hips. The touch of both men made your skin sizzle with anticipation, and when Dean pulled away, jerking his head towards the bed, you found yourself unable to argue. Especially when Cas followed you down, continuing to kiss you, but this time finding your nipples with his teeth and tongue. You gasped loudly, and Dean smiled at the reaction. 'Thought you said you’d never been with a woman, Cas?’

'I’m merely drawing from experience of what you like.’ Cas said, pulling his head away from your breast, making you moan in protest. 'It is a simple process – she seems more sensitive that you do though.’

'Women tend to have more sensitivity in that general area.’ Dean moved closer, reaching out a hand to gently caress the top of your breast. You arch into his touch, and Cas watched with interest. 'Like this -’ He tweaked your nipple with his forefinger and thumb, rolling it between the digits as you cried out. 'She likes it.’ Cas tilted his head to the side, then repeated Dean’s actions on your other breast. Your cries became louder, and you panted, wondering how intense this was going to get if both of them were doing the same thing. Then Dean’s words came back to you, and the thought of seeing him fuck Cas was a little too much to bear.

'I think I understand.’ Cas murmured, and Dean removed his fingers from your breast, smiling as Cas lowered his mouth to it, and you continued to squirm under his touch. A few moments passed where Dean just watched, his hand stroking over the bulge in his pants.

'Cas.’ He said, his voice lower than it had been before, and thick with lust. 'Take her pants off.’ He paused. 'Then take yours off.’ The angel stopped what he was doing, looking up at Dean, then over to you, and his hands went to your pants, unbuttoning them and pulling them down over your legs. 'Panties too.’ Dean added, and Cas obliged, leaving you exposed to their view. You fought the urge to cover up, feeling incredibly self conscious, and Dean seemed to notice this, shaking his head as Cas unbuttoned his own pants. 'Trust me, Y/N, you’re not gonna care in about five seconds.’ He moved around the bed, pushing his own trousers down as he did. Cas was fully naked now, standing by the side of the bed, looking down at you, but you were staring at Dean, who’d removed the rest of his clothes and was climbing onto the bed next to you. He smiled, seemingly aware of your gaze lingering on his hard cock, and he pulled at your hip with his hand. 'Come here.’ He motioned and you nodded dumbly, pulling yourself up. 'I want you to sit on my face.’ Your eyes widened a little, and he laughed. 'Don’t worry. You’ll enjoy it.’ He laid down, pulling you over to him and you reluctantly straddled his shoulders, his mouth centimetres away from your already wet pussy. You felt the bed shift as Cas knelt between Dean’s legs, but every single coherent thought you had was soon obliterated as Dean’s tongue flicked out against your clit, and you almost collapsed right there. He moaned into your quim, stroking up and down with his tongue, catching your clit with every upward motion and you forgot whatever reservations had been left over. Over your shoulder, you saw Cas bend down, and Dean grunted, the vibrations intense against you, and you realised that whilst he was licking you out, Cas was sucking his cock. You were suddenly curious to see, and not only a little horny, and Dean’s moan were only furthering that as he moved his hand to plunge a single finger inside you.

'Fuck, Cas.’ Dean’s eyes closed as he finger fucked you, the feeling of the angel’s hot mouth around his cock making him unable to concentrate momentarily. Your own thoughts were all over the place as Dean worked you over with his hand, and you longer to see what Cas was doing to the man underneath you both. Dean’s movements stilled, and you took the opportunity, ignoring your own need for release as you climbed off of him to turn and see Cas practically devouring Dean’s cock. Dean didn’t even seem to notice that you’d moved, his eyes shut, one hand fisted in the bedclothes. Cas opened his eyes to look up at you, his mouth full of cock, and you smiled, coming closer. Cas released the hunter with a soft wet plop, his hand remaining around the base, and Dean grunted at the loss of his mouth. 'Fuck why’d you -’ His eyes went to you, but you weren’t looking at him. As if in tandem, you and Cas attacked together, your hand holding Dean down by his chest, both of your mouths working on his cock and his cry of pleasure sent a jolt of electricity to your cunt. He repeated a litany of curses as you both went down on him, licking, sucking, occasionally nipping at him, taking it in turns to deep throat him.

After a few moments, Dean pushed back against your hand, and you stopped, Cas following suit, and the hunter sat up on the bed, looking at you both. His eyes were lidded and darkened, and he pointed at Cas. 'I’m gonna fuck you. And you’re gonna fuck her.’

The angel nodded, and you felt heat and moisture pool between your legs. 'Lay down.’ Dean commanded, and you obeyed, taking his place on the bed, Cas hovering over you, as the other man moved to kneel behind Cas, placing a soft kiss between his shoulder blades. He reached under the bed, grabbing out a bottle of lube from his bag. He didn’t apply any yet, but he held Cas close to his chest, gesturing to you as you lay prostate beneath them. 'I want you to finger her. Make her cum, Cas.’

Cas nodded, slightly breathlessly, and his hands rested on your thighs, parting them gently. He traced your pussy lips with his forefinger, smiling at the way you arched into his touch. Slowly, he pushed one finger inside you, curling it upwards and you briefly wondered if he was drawing on previous experience with Dean for this too. Adding another finger, he pressed harder, thrusting his fingers in and out, hitting that sweet spot inside you, and your body tensed, your cunt tightening as he continued the actions. You were so close to cumming, and then he froze, and you opened your eyes, seeing his face in complete bliss as he slowly began to resume his movements within you. Dean’s face was pressed against his shoulder, and his arm was moving. He looked over at you, a sly smile on his face.

'He can finger you, while I’m…’ Cas cried out, interrupting his words, and you guessed exactly what Dean was doing to him.

And that pushed you over the edge, the angel’s fingers making you buckle and cry out, mimicking him as you came hard.

'Fuck, Cas. Want you. Take her.’ Dean muttered, and Cas nodded, swallowing hard as he removed his hand from your pussy, allowing Dean to push him forward, his cock brushing against you. His hand wrapped around his member, and he lined himself up, pushing into you slowly. Dean watched for a moment as your eyes rolled back in your head, your mouth falling open in an “o”, as Cas filled you to breaking point. 'Stay still.’ He ordered, lubing up his own cock and shifting slightly so he was against Cas’ ass. He placed a hand against the angel’s lower back, his other hand wrapped around his cock, and he kept his eyes on you as he pushed into the angel slowly, Cas’ head rearing back as the hunter penetrated him. The action pushed him further into you and you gasped for air.

'Fuck.’ Cas muttered, his hands pinning yours to the bed. Your cunt clenched around him, and then Dean moved, pulling back out and pushing back in once more. Cas’ moan was deep, and again, Dean’s actions pushed him further into you. He started moving more vigorously, his hands around Cas’s hips, manoeuvring the angel so he was fucking you whilst he was being fucked.

'Does that feel good?’ Dean asked, his hair sticking to his forehead as he pounded into the angel, and subsequently, you. The extra pressure made each thrust hit you in places you didn’t know could be hit, and you cried out each time, nodded sporadically at Dean’s questions. Cas didn’t even try to answer, the double sensations of being fucked by Dean and fucking you too much for him to handle, and Dean seemed to sense it, slowing his thrusts. 'You okay?’ He asked, and Cas threw a glare over his shoulder.

'I did not say stop.’

The grin that spilled over Dean’s face was contagious, but as you felt your release coming, you stopped paying attention to either of the guys, and focused on the sensations coursing through you. Every nerve ending in your body was on fire, and your cries mingled with those of the boys as all three of you spiralled out of control. Fireworks exploded in your mind as you came hard, and pulled Cas over the edge with you. Dean continued to fuck him hard, the shock waves of each thrust pushing his still hard dick into you, prolonging your orgasm to immeasurable lengths as you cried out, your throat sore and voice hoarse. Cas was practically whimpering now, and as Dean grunted out his orgasm, spilling into Cas as the angel took every thrust from the hunter until he finished.

All three of you collapsed in a messy heap on the motel room bed, heavy pants mingling together as Dean pulled out and away from Cas, the angel gasping at the loss. You felt pleasurably numb as you felt Cas curl inside your side, the bed dipping as Dean moved away to clean up. You moved your head, feeling sleep beckoning to you as you looked down at the exhausted angel to your side. 'So…’

'That was extremely enjoyable.’ He muttered, seemly unable to keep his blue eyes open as his hand snaked over your stomach. You smiled languidly as Dean returned to the bed, sitting on your other side, an affectionate grin on his face as he bent to kiss you quickly.

'I said it wouldn’t be weird.’ He muttered, and you chuckled in response.

'No. It was just…wonderful.’


End file.
